CN105301901A - Preparation method of positive photoresist composition - Google Patents
Preparation method of positive photoresist composition Download PDFInfo
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- CN105301901A CN105301901A CN201510781931.4A CN201510781931A CN105301901A CN 105301901 A CN105301901 A CN 105301901A CN 201510781931 A CN201510781931 A CN 201510781931A CN 105301901 A CN105301901 A CN 105301901A
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- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229920002120 photoresistant polymer Polymers 0.000 title abstract description 34
- 239000013543 active substance Substances 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 12
- 239000011347 resin Substances 0.000 claims abstract description 12
- 238000001259 photo etching Methods 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 230000003287 optical effect Effects 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 12
- 229940113088 dimethylacetamide Drugs 0.000 claims description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 12
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 10
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 10
- 239000003292 glue Substances 0.000 claims description 10
- NHRMHEKXRUSPAE-UHFFFAOYSA-N methyl 4-hydroxy-2-methylidenebutanoate Chemical class COC(=O)C(=C)CCO NHRMHEKXRUSPAE-UHFFFAOYSA-N 0.000 claims description 10
- IAGVANYWTGRDOU-UHFFFAOYSA-N 1,4-dioxonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C(S(=O)(=O)O)=CC(=O)C2=C1 IAGVANYWTGRDOU-UHFFFAOYSA-N 0.000 claims description 9
- 239000012954 diazonium Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- -1 and before exposure Chemical compound 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
Landscapes
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention discloses a preparation method of a positive photoresist composition. The method comprises the following step: (1) fetching a solvent for dissolving a photolytic active substance, uniformly stirring for obtaining a photolytic active substance solution; (2) heating a photolytic active substance solution to 50-54 DEG C, adding a polyether modified organosilicon flatting agent and resin, and uniformly mixing at a constant temperature; (3) a heating is carried out to 80-83 DEG C, an isothermal stirring is carried out for two hours for removing solvents, and the photoresist composition is obtained. The prepared photoresist has a high photosensitive speed, and the image obtained by photoetching has a high resolution.
Description
Technical field
The invention belongs to Other substrate materials technical field, be specifically related to a kind of preparation method of positive-tone photo glue composition.
Background technology
Photoresist refers to that a large class has the macromolecule polymer material of photosensitizing chemical effect (or responsive to electron energy), is resist again, is also photoresist.Be mainly used in integrated circuit, encapsulation, MEMS (micro electro mechanical system), optoelectronic device photonic device, flat-panel monitor, the fields such as photovoltaic.After illumination, can there is photocuring reaction in exposure region in photosensitive resin, make the physical property of this material soon, and particularly significant change occurs for dissolubility, affinity etc.Through suitable solvent process, dissolve soluble part, obtain required image.The technical sophistication of photoresist, kind is more.According to its chemical reaction mechanism and development principle, negative photoresist and positive photoresist two class can be divided.What form insoluble material after illumination is negative photoresist; Otherwise be insoluble to some solvent, what become soluble substance after illumination is positive photoresist.Utilize this performance, by photoresist making coatings, the circuitous pattern needed for just etching at silicon chip surface.
Photoresist consist of resin, the bonding agent of different materials in photoresist, give with the machinery of photoresist and chemical property that (as emulsion such as adhesiveness, film thickness, thermal stabilitys, emulsion is to luminous energy generation photochemical reaction; Solvent, keeps the liquid condition of photoresist, makes it to have good mobility; Adjuvant, in order to change some characteristic of photoresist, adds coloring agent etc. as improved photoresist that reflection occurs.Negative photoresist: resin is polyisoprene, a kind of natural rubber; Solvent is dimethylbenzene; Emulsion is a kind of photosensitizer discharging nitrogen after overexposure, and the free radical of generation is formed crosslinked between rubber molecule.Thus become and be insoluble to developer solution.Negative photoresist causes bubble to rise in exposure region by solvent; During exposure, photoresist easily reacts with nitrogen and suppresses to be cross-linked.Positive photoresist: resin is a kind of phenolic aldehyde formaldehyde being called linear phenolic resin, provides the adhesiveness of photoresist, chemical resistance, and when not having dissolution inhibitor, linear phenolic resin can be dissolved in developer solution; Emulsion is light-sensitive compound, and modal is diazo naphthoquinone, and before exposure, diazo naphthoquinone is a kind of strong dissolution inhibitor, reduces the dissolution velocity of resin.After uv-exposure, diazo naphthoquinone is chemolysis in the photoresist, becomes solubility enhancing agent, significantly improves the solubleness factor to 100 in developer solution or higher.This exposure reaction can produce carboxylic acid in diazo naphthoquinone, and its solubleness in developer solution is very high.Positive photoresist has good contrast, so the figure generated has good resolution.
In existing technology, photoresist is after the pyroprocessing of rear baking, and film surface is easy to shrink, and makes photoresist crawling.When being applied to gene order-checking like this, photoresist is coated on chip, can affect accuracy of detection, causes result inaccurate.
Summary of the invention
An object of the present invention is a kind of preparation method of positive-tone photo glue composition, comprise the following steps:
(1) get dissolution with solvents optical active substance, stir, obtain optical active substance solution;
(2) optical active substance solution warms is to 50-54 DEG C, and add polyether-modified organosilicon levelling agent and resin, constant temperature mixes;
(3) be warming up to 80-83 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
Described composition is by weight being polyether-modified organosilicon levelling agent 0.4-0.55 part, solvent 22-25 part, optical active substance 2-3 part and resin 16-18 part.
Described polyether-modified organosilicon levelling agent is ETA-735.
Described solvent is tetrahydrofuran, 1-Methoxy-2-propyl acetate and dimethyl acetamide.
The weight ratio of described tetrahydrofuran, 1-Methoxy-2-propyl acetate and dimethyl acetamide is (4-5): (13-16): (4-7).
The weight ratio of described tetrahydrofuran, 1-Methoxy-2-propyl acetate and dimethyl acetamide is 4:16:5.
Described optical active substance is diazonium naphthoquinone sulphonate.
Described resin is 2-hydroxyethylacrylate methyl esters, trimethylol-propane trimethacrylate and n-BMA, and the weight ratio of 2-hydroxyethylacrylate methyl esters, trimethylol-propane trimethacrylate and n-BMA is 3:1:6.
With the addition of polyether-modified organosilicon levelling agent ETA-735 in positive photoresist in the present invention, coat on chip, the even film layer obtained, level and smooth.The photoresist prepared is applicable to coating on the genetic chip in gene order-checking very much, makes testing result precision high, can carry out large-scale industrial production.Positive photoresist in the present invention has very high film speed, and the image resolution ratio that photoetching obtains is high, is very suitable for large-scale promotion application.
Embodiment
embodiment 1
(1) get solvents tetrahydrofurane 4 parts, 1-Methoxy-2-propyl acetate 16 parts and dimethyl acetamide 5 parts and dissolve diazonium naphthoquinone sulphonate 2 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 50 DEG C, add ETA-7350.4 part, 2-hydroxyethylacrylate methyl esters 4 parts, trimethylol-propane trimethacrylate 2 parts and n-BMA 12 parts, constant temperature mixes;
(3) be warming up to 80 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
embodiment 2
(1) get solvents tetrahydrofurane 4 parts, 1-Methoxy-2-propyl acetate 14 parts and dimethyl acetamide 4 parts and dissolve diazonium naphthoquinone sulphonate 2 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 54 DEG C, add ETA-7350.55 part, 2-hydroxyethylacrylate methyl esters 3 parts, trimethylol-propane trimethacrylate 3 parts and n-BMA 10 parts, constant temperature mixes;
(3) be warming up to 83 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
embodiment 3
(1) get solvents tetrahydrofurane 4 parts, 1-Methoxy-2-propyl acetate 14 parts and dimethyl acetamide 7 parts and dissolve diazonium naphthoquinone sulphonate 2 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 52 DEG C, add ETA-7350.5 part, 2-hydroxyethylacrylate methyl esters 5 parts, trimethylol-propane trimethacrylate 8 parts and n-BMA 4 parts, constant temperature mixes;
(3) be warming up to 81 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
embodiment 4
(1) get solvents tetrahydrofurane 4.5 parts, 1-Methoxy-2-propyl acetate 13 parts and dimethyl acetamide 6.5 parts and dissolve diazonium naphthoquinone sulphonate 3 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 52 DEG C, add ETA-7350.45 part, 2-hydroxyethylacrylate methyl esters 5 parts, trimethylol-propane trimethacrylate 8 parts and n-BMA 4 parts, constant temperature mixes;
(3) be warming up to 80 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
embodiment 5
(1) get solvents tetrahydrofurane 5 parts, 1-Methoxy-2-propyl acetate 14 parts and dimethyl acetamide 5 parts and dissolve diazonium naphthoquinone sulphonate 3 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 52 DEG C, add ETA-7350.48 part, 2-hydroxyethylacrylate methyl esters 9 parts, trimethylol-propane trimethacrylate 4 parts and n-BMA 4 parts, constant temperature mixes;
(3) be warming up to 82 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
embodiment 6
(1) get solvents tetrahydrofurane 5 parts, 1-Methoxy-2-propyl acetate 15 parts and dimethyl acetamide 5 parts and dissolve diazonium naphthoquinone sulphonate 2.5 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 53 DEG C, add ETA-7350.42 part, 2-hydroxyethylacrylate methyl esters 8 parts, trimethylol-propane trimethacrylate 5 parts and n-BMA 4 parts, constant temperature mixes;
(4) be warming up to 82.5 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
comparative example
(1) get solvents tetrahydrofurane 8 parts, 1-Methoxy-2-propyl acetate 2 parts and dimethyl acetamide 0.5 part and dissolve diazonium naphthoquinone sulphonate 2 parts, stir, obtain optical active substance solution;
(2) optical active substance solution warms to 52.5 DEG C, add ETA-7350.4 part, 2-hydroxyethylacrylate methyl esters 4 parts, trimethylol-propane trimethacrylate 2 parts and n-BMA 4 parts, constant temperature mixes;
(4) be warming up to 60 DEG C, constant temperature stirs 1 hour with except desolventizing, obtains photoetching compositions.
experimental example
Photoresist of the present invention is coated in chip substrates as liquid coating composition, until coating is no longer sticked together, by photomask exposure under activation is irradiated, with alkaline-based developer development, forms camegraph.Measure the film speed of embodiment 1-embodiment 4 and comparative example photoresist after the production immediately, result is as table 1:
Table 1
As shown in Table 1, the film speed of the obtained photoresist of embodiment of the present invention 1-embodiment 4 is significantly higher than comparative example, and its quality smooth uniform, quality is high.
Above-mentioned detailed description is illustrating for one of them possible embodiments of the present invention, and this embodiment is also not used to limit the scope of the claims of the present invention, and the equivalence that all the present invention of disengaging do is implemented or changed, and all should be contained in the scope of technical solution of the present invention.
Claims (7)
1. a preparation method for positive-tone photo glue composition, is characterized in that, comprises the following steps:
(1) get dissolution with solvents optical active substance, stir, obtain optical active substance solution;
(2) optical active substance solution warms is to 50-54 DEG C, and add polyether-modified organosilicon levelling agent and resin, constant temperature mixes;
(3) be warming up to 80-83 DEG C, constant temperature stirs two hours with except desolventizing, obtains photoetching compositions.
2. the preparation method of positive-tone photo glue composition as claimed in claim 1, is characterized in that, described composition is by weight being polyether-modified organosilicon levelling agent 0.4-0.55 part, solvent 22-25 part, optical active substance 2-3 part and resin 16-18 part.
3. the preparation method of positive-tone photo glue composition as claimed in claim 1, it is characterized in that, described polyether-modified organosilicon levelling agent is ETA-735.
4. the preparation method of positive-tone photo glue composition as claimed in claim 1, it is characterized in that, described solvent is tetrahydrofuran, 1-Methoxy-2-propyl acetate and dimethyl acetamide.
5. the preparation method of positive-tone photo glue composition as claimed in claim 1, it is characterized in that, the weight ratio of described tetrahydrofuran, 1-Methoxy-2-propyl acetate and dimethyl acetamide is (4-6): (13-16): (4-7).
6. the preparation method of positive-tone photo glue composition as claimed in claim 1, it is characterized in that, described optical active substance is diazonium naphthoquinone sulphonate.
7. the preparation method of positive-tone photo glue composition as claimed in claim 1, it is characterized in that, described resin is 2-hydroxyethylacrylate methyl esters, trimethylol-propane trimethacrylate and n-BMA.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510781931.4A CN105301901A (en) | 2015-11-16 | 2015-11-16 | Preparation method of positive photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510781931.4A CN105301901A (en) | 2015-11-16 | 2015-11-16 | Preparation method of positive photoresist composition |
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| Publication Number | Publication Date |
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| CN105301901A true CN105301901A (en) | 2016-02-03 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201510781931.4A Pending CN105301901A (en) | 2015-11-16 | 2015-11-16 | Preparation method of positive photoresist composition |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112485967A (en) * | 2020-12-29 | 2021-03-12 | 安徽邦铭新材料科技有限公司 | Photoresist composition for TFT-LCD |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001100406A (en) * | 1999-09-27 | 2001-04-13 | Tokyo Ohka Kogyo Co Ltd | Positive type photoresist composutuon, substrate withh photosensitive film and resist patten forming method |
| CN1786752A (en) * | 2004-12-07 | 2006-06-14 | 东进世美肯株式会社 | Photosensitive resin composition for color filter and method for mfg. LCD color filter by same |
| CN1814675A (en) * | 2005-02-02 | 2006-08-09 | 东洋油墨制造株式会社 | Coloring composition,Color filter within this and its producing method |
| CN101770169A (en) * | 2008-12-30 | 2010-07-07 | 乐凯集团第二胶片厂 | Positive lithograph plate photosensitive composition with high resolution and high sensitivity |
| CN103180784A (en) * | 2010-09-02 | 2013-06-26 | 东丽株式会社 | Photosensitive composition, cured film formed from same, and element having cured film |
| CN103792789A (en) * | 2014-01-27 | 2014-05-14 | 京东方科技集团股份有限公司 | Photoresist composition |
-
2015
- 2015-11-16 CN CN201510781931.4A patent/CN105301901A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001100406A (en) * | 1999-09-27 | 2001-04-13 | Tokyo Ohka Kogyo Co Ltd | Positive type photoresist composutuon, substrate withh photosensitive film and resist patten forming method |
| CN1786752A (en) * | 2004-12-07 | 2006-06-14 | 东进世美肯株式会社 | Photosensitive resin composition for color filter and method for mfg. LCD color filter by same |
| CN1814675A (en) * | 2005-02-02 | 2006-08-09 | 东洋油墨制造株式会社 | Coloring composition,Color filter within this and its producing method |
| CN101770169A (en) * | 2008-12-30 | 2010-07-07 | 乐凯集团第二胶片厂 | Positive lithograph plate photosensitive composition with high resolution and high sensitivity |
| CN103180784A (en) * | 2010-09-02 | 2013-06-26 | 东丽株式会社 | Photosensitive composition, cured film formed from same, and element having cured film |
| CN103792789A (en) * | 2014-01-27 | 2014-05-14 | 京东方科技集团股份有限公司 | Photoresist composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112485967A (en) * | 2020-12-29 | 2021-03-12 | 安徽邦铭新材料科技有限公司 | Photoresist composition for TFT-LCD |
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